Acetic Acid → (2S,4S)-2-(2-fluoroethyloxymethyl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

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Reaction Steps

To a solution of (2S,4S)-4-acetylthio-2-(2-fluoroethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.70 g) in methanol (35 ml) was dropwise added a 28% solution (1.2 ml) of sodium methoxide in methanol at -10°~-5° C. in a nitrogen stream, followed by stirring at the same temperature for 1 hour. To the mixture was added acetic acid (0.4 ml) at -10°~-5° C. The mixture was concentrated under reduced pressure to give a residue. The residue was poured into a mixture of water (50 ml) and ethyl acetate (50 ml). The organic layer was separated, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (25 g) and eluted with chloroform to give (2S,4S)-2-(2-fluoroethyloxymethyl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.91 g).

Provenance & Evidence